Home > Riverside > 1357 Osceola Dr, Fort Myers, FL 33901
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1357 Osceola Dr, Fort Myers, FL 33901 - 5 Bedroom Pool Home in Riverside

$1,150,000

MLS Number
2026022632
Bedrooms
5 Bed
Bathrooms
3 Baths + 1 Half
Living Area
3,928 sq ft
Total Area
8,377 sq ft
Garage Spaces
2
Year Built
2000
Days on Market
23

home Property Description

Welcome to this fabulous estate home located in one of the area’s most sought-after neighborhoods, just moments from the historic Edison & Ford Winter Estates. Located one block from the beautiful Caloosahatchee River. Situated outside of a designated flood zone, this property offers the added peace of mind and convenience of no required flood insurance.

This expansive residence offers over 3,900 square feet of living space with five bedrooms and three-and-a-half bathrooms, designed perfectly for a large family or anyone who loves to entertain.

As you enter through the elegant French glass front doors from the charming front porch, you are welcomed by a spacious and inviting layout. To the right, you’ll find a beautiful formal living room or den, while the left side features an elegant dining room perfect for gatherings and holiday dinners.

The heart of the home is the stunning open-concept kitchen, showcasing glass-front cabinetry, beautiful appliances, and generous space for entertaining, all flowing seamlessly into the oversized family room.

The split floor plan offers privacy and functionality. On the right side of the home, you’ll find three spacious bedrooms and two full bathrooms. On the opposite wing, the luxurious primary suite features a cozy double-sided fireplace connecting the bedroom and spa-inspired bathroom, complete with a soaking tub and separate shower. The primary suite also offers direct access to the pool area. An additional bedroom and bathroom are also located on this side of the home.

Step outside to your enormous outdoor living space, featuring a sparkling pool surrounded by beautiful travertine tile, creating the perfect Florida retreat for relaxing or entertaining guests.

The property also includes a detached garage with endless possibilities—ideal for a mother-in-law suite conversion, private guest retreat, antique car storage, or whatever your vision may be. An additional flex space currently serves as an impressive home gym but could easily be transformed into a studio, office, or recreational area.

Additional highlights include gorgeous oak and tile flooring throughout, breathtaking mature oak trees in the front yard, and an unbeatable location just minutes from Downtown Fort Myers dining, shopping, and entertainment.

Located just minutes from Downtown Fort Myers, you’ll enjoy quick access to waterfront dining, live music, shopping, breweries, art walks, and community events. Spend weekends exploring the River District, catching sunsets along the water, visiting nearby marinas, or taking a short drive to Southwest Florida’s beautiful beaches, golf courses, and nature preserves.

Rarely does a home combine this much space, versatility, charm, and location in one extraordinary package. This is more than just a home—it’s a lifestyle opportunity to experience the very best of Southwest Florida living.

fact_check The Basics

Property Type Single Family
Gulf Access No
Private Pool Yes
Private Spa No
Acres 0.638
Furnished Unfurnished
Last Modified 2 weeks ago

savings Financials & HOA Fees

Foreclosure No
Auction No
Short Sale No
Mandatory HOA No

roofing Building Features

Building Features DSL/Cable Available
Building Style 1 Story/Ranch
Construction Materials Concrete Block, Stucco
Cooling Ceiling Fan(s), Central Electric
Covered Spaces 3
Elevator None
Floor Plan Great Room, Split Bedrooms
Floors 1
Garage Spaces 2
Patio and Porch Patio
Other Structures Storage
Rear Exposure North
Roof Shingle
Security Features Smoke Detector(s)
Storm Protection None
View Landscaped Area
Water Source Assessment Paid, Central

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chair Interior Features

Appliances & Equipment Auto Garage Door, Cooktop, Cooktop - Electric, Dishwasher, Disposal, Dryer, Ice Maker - Stand Alone, Refrigerator/Icemaker, Smoke Detector, Trash Compactor, Washer
Interior Features Built-In Cabinets, Fireplace, Foyer, French Doors, Laundry Tub, Pantry, Smoke Detectors, Tray Ceiling(s), Walk-In Closet(s)
Additional Rooms Den - Study, Exercise, Family Room, Great Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Open Porch/Lanai, Screened Balcony, Screened Lanai/Porch
Kitchen Features Island, Walk-In Pantry
Flooring Carpet, Tile, Wood
Gas No
Laundry Laundry in Residence, Laundry Tub

holiday_village Neighborhood and Community

Pets Allowed Yes
Amenities Fitness Center, Storage, Guest Room, Hobby Room, Internet Access
Neighborhood Riverside
Neighborhood Type Non-Gated
Community Features Fitness Center
Included in Fees None
HOA Restrictions Deeded

photo_library Additional Images

Chris Farrugia, REALTOR Portrait

Chris Farrugia, M.B.A.

Realtor® at The Listing Naples Group

📞 (239) 248-8171
📧 chris@listingnaples.com

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The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

Listing provided by RE/MAX Trend.